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New Member

Add me to the list of folks who can't sync their iPhone to Outlook. After installing iTunes 7.3, whenever I launch Outlook (ver 2007), I get the application crash window (with the option to send an error report) followed by another message box that reads "Outlook experienced a serious problem with the 'outlook iTunes sync addin' add-in...", then it asks me if I want to disable the addin. The only way Outlook will run is if I disable the addin. But then I can't sync! I re-enabled the addin, but Outlook simply crashes again. Anyone else have this problem and found a workaround?

New Member

I was using Entourage on a Mac but changed to the Apple suite of applications as I figured there would be problems syncing. I'd been down that road with my Palm Pilot before! Anyhow, I'm having trouble syncing my iPhone with iCal so that the begin and end times show up correctly. The events show up but the times listed are always five hours off. If I enter an event in iCal on my computer and then sync it shows up five hours later on my iPhone. If I enter it on my iPhone and sync it shows up five hours earlier in iCal. I've checked my time zones but they are set to Central. I've reset my iPhone software but that didn't work. I heard using ampersands "&" can cause problems with iCal syncs so I removed them. I've tried exporting and re-importing data to no avail. I've even completely backed up, zeroed out my disk, and re-formatted my computer. Still the same thing. Finally I checked a friends computer and he had the same thing happen except his events were consistently 6 hours off. Very puzzling and disappointing since I was really hpoing to use this feature to organize my schedule. It appears to be a software problem but I'd still sincerely appreciate any ideas or suggestions to try and fix this. I was about to put my Palm Pilot on eBay but think I better hold on to it for awhile!

New Member

Good news, for me, that is. I gave up trying to sync Outlook on my desktop Windows XP machine. I switched to my Windows XP laptop and now everything works. I was able to sync my Outlook email accounts, contacts, calendar (yes, even the calendar synced), Explorer bookmarks, all that junk. I dunno, something on my XP desktop must be causing some sort of conflict between Outlook and iTunes. At some point I may rebuild the desktop machine (something you Mac folks aren't familiar with!), but that's a lot of work.

New Member

I tried adding iTunes to the ignore list, but I still can't sync. The add-in seems to have been permanently disabled from Outlook. I try to re-enable it, apply the changes, but when I view the add-in settings again, it's disabled. I even tried adding both Outlook and and iTunes to the DEP ignore, but the add-in still cannot be re-enabled and sync still doesn't work. I tried reinstalling iTunes, no change. I'll just stick with my laptop solution. Good luck with yours...

New Member

New Member

Yes but Outlook 2003 disables one of the add-ins which causes Outlook to crash when you load program. Then the add-in is disabled and you can't enable it just by selecting the box in tools>other>advanced>com add-ins because it won't happen.It just keeps unchecking itself.
Here's what to do: with outlook open go to "about Outlook" You'll see a button "disabled components" under that will be the offending iPhone addin. RE-enable it. Then do the manouevre I mentioned in second sentence. Then sync iPhone and all contacts, calendar etc will sync to phone. BUT the next time you start up Outlook it will tell you that the addin causes a serious error and will disable it. I guess we will have to enable it each time we want to sync for now -Microsoft had no idea (nor did Apple) after several hours on support lines. God only knows when and who will fix this. This seems to work for now however.

New Member

WOW! It actually works! Following dscales and reidsch's advice, I added iTunes to the DEP exclude (reidsch's advice) and re-enabled the add-in (dscales' advice), and it WORKS! As an added bonus, the iTunes add-in no longer crashes Outlook, so I don't have to keep re-enabling it. Thanks!

New Member

It is official we are not the only folks that got this issue - check out http://www.geekzone.co.nz/juha/3253 this guys sees things exactly as I see them. I have beena ble to digg out more stuff here. The issue goes back to two .DLL files. They are the followings:

A) Outlooksyncclient.dll
B) Ituneoutlookaddin.dll

You can go to Outlook and check this out:

Tools>Trust Center>Add Ins ....

Checkout the list that comes out as the result. You will see that iTune has added two files at two different locations just about the same time .. but the main error message called out by Geekzone post is pointing to file "A" in my list. By now I have reinstalled Outlook 2007, iTune 7.3 multiple times and no result. So, I can say this - those that have tried this and got it working for them - must have been darn lucky - as this software seems really bugy to me and still cannot get any responce from Apple on this. Will post more as I learn more.

New Member

Yes but Outlook 2003 disables one of the add-ins which causes Outlook to crash when you load program. Then the add-in is disabled and you can't enable it just by selecting the box in tools>other>advanced>com add-ins because it won't happen.It just keeps unchecking itself.
Here's what to do: with outlook open go to "about Outlook" You'll see a button "disabled components" under that will be the offending iPhone addin. RE-enable it. Then do the manouevre I mentioned in second sentence. Then sync iPhone and all contacts, calendar etc will sync to phone. BUT the next time you start up Outlook it will tell you that the addin causes a serious error and will disable it. I guess we will have to enable it each time we want to sync for now -Microsoft had no idea (nor did Apple) after several hours on support lines. God only knows when and who will fix this. This seems to work for now however.

New Member

Many thanks for sharing ... I tried to follow the steps you shared here. Couple of observation - Outlook 2007, my version, has got no item under Tools-Options-other that is got anything to do with Add-In MGMT ... I look for it for number of hours and I can tell you that in 2007 ... no such thing exist. The only thing ths is there and I can use is Trust Center under tools which in turn allows you get the list of Comm. Addins so I can disable the two Plug-Ins that iTune putts in ones machine. After enabling only one of the plug-Ins ... I tried to sych and my calendar still does not not sycn. So, I will just keep on trying ... and let us know if you find any new tricks.

New Member

at the bottom, there's a list box. if you scroll to "Disabled Items" and hit "Go", you'll see a pop up with the offending add-in. Highlight this and hit "Enable". you'll then have to restart Outlook and the cycle starts over; Outlook freezes and asks you to deactivate.

Now, i've been able to sync from Outlook2007 from my laptop and my work pc, but not my home pc due to these issues stated above. So, on a hunch, i backed up my PST file at home, and created a "new" account with my same credentials, effectively creating a new PST data file. i re-imported my calendar and contacts.

When i tried to sync... it worked perfectly. So the problem, thereforee, lies in the data file. could it be file structures? too many emails? to large a data file? some formatting thing? who knows? but if everyone tries this, i'll bet more than a few will find this to work. the only drawback is that in this new PST data file, you won't have your old emails and file structure.

New Member

I am running WindowsXP SP2 and Outlook 2003 and still unable to get the following DLL to load correctly in Outlook without crashing it:
C:\Program Files\Common Files\Apple\Mobile Device Support\bin\OutlookSyncClient.dll

This is a pain and deep down I knew this would happen when I wanted an iPhone but didn't have a Mac.

If anyone has an update on this please let me know this is such a pain and frustration that I cannot sync my calendar and contacts from outlook which I used to be able to do seemlessly with my Windows Mobile Phone.

New Member

I am running WindowsXP SP2 and Outlook 2003 and still unable to get the following DLL to load correctly in Outlook without crashing it:
C:\Program Files\Common Files\Apple\Mobile Device Support\bin\OutlookSyncClient.dll

New Member

I tried everything suggested here to no avail. Outlook crashed every time i OPENED it as long as the iTunes sync plug-in was enabled.

Someone else suggested that perhaps the problem was a large PST file. Mine had grown to over 6 GB, so I tried creating a brand-new one and switched Outlook over to use the new PST for default mail delivery. I was then able to immediately sync with iTunes. Clearly iTunes has a problem with large PSTs or perhaps there was some subtle corruption in the PST which Outlook didn't care about but hung iTunes up. I deleted some email and compressed my original PST and was able to get it to work again. My revised PST is at about 4 GB and things seem to be working.

New Member

I tried to create a new Outlook profile and was still unable to sync with Outlook....I wish my issue was that simple. I think my PST is only around 300 MBs and I have my 2 Gmail accounts and my Hotmail account setup on it. However on my new profile, I had a brand new PST and only 1 gmail account and still errored out due to the outlooksyncclient.dll plug-in.